Disazo dyestuffs



Patented Aug. 15, 1939 PATENT orries DISAZO- DYESTUFFS "Wolfgang Alt and Hans Krzikalla, Ludwigsha- 'fen-on-the-Rhine, Germany,

assignors to General Aniline Works, Inc., New York, N. Y., a corporation of Delaware No Drawing. Application October 20, 1938, Se-

rial No. 236,034. In Germany November 19,

5- Claims.

The present invention relates to disazo dyestuffs, a process of producing same and a process of dyeing textile materials therewith.

We have found that disa'zo dyestufls having valuable properties are obtained by causing diazo compounds of aromatic amines to react with ortho-hydroxy-aryl carboxylic arylides containing at least one sulfonic acid group in the arylide portion, which corresponds to the following formula on HO p Ar XAI CONHB1-NH-BrNH-BaNH-CO wherein the Ar stands for arylene radicles, and wherein B1, B2 and B3 stand for phenylene radicles.

Arylides of this type may beprepared for example by reacting two molecular proportions of an ortho-hydroxy-aryl carboxylic acid, e., g. 2-hydroxynaphthalene 3 5 carboxylic acid, their chlorides, their 'ortho-acyloxy chlorides or their esters with one molecular proportion of an N,N di- (aminophenyl) -diamino-benzene sulfonic acid corresponding to the general formula wherein B1, B2 and B3 represents phenylene radicles at 'least'one'of which contains a sulfonic' acid group. These diamines may be prepared by condensing phenylene-diamines, e. g. paraor metaphenylene diamine ortoluylene diamines, with paraor orthonitrochlorbengene sulfonic acids which may be further substituted for example by alkyl or alkoxy groups or additional acid and 7.8-benzocarbazole-Bz.3-hydroxy-2-carboxylic acid. v v

As diazo components for the process according to this invention there may be mentioned the usual amines employed in the preparation of azo dyestuffs, inparticular those not containing solubilising groups, such as aniline, nitroaminor the fibre and developing them thereon by treatment with diazo-compounds.

The coupling components have alfinity for animal fibres and they also go onto vegetable fibres. It is, therefore, possible to produce on mixtures of dilferent fibres, as for example on mixed yarns or mixed fabrics, especially those of wool and regenerated cellulose (staple fibre) very fast dyeings, exceptionally level on both kinds of fibres.

The following example will further illustrate how our invention may be carried out in practice but the invention is not restricted to this example.

' Example A mixed fabric of 50 per cent of wool and 50 percent ofstaple fibre (viscose silk). is treated for an hour at C. in a bath with a bath ratio of 1:20 with 3 per cent of the disodium salt of the composition:

CONHQNHGNHQNHCO halogen atoms, and reducing the dinitro compounds toform diamines.

For the preparation of the arylides there may be mentioned in particular 2-hydroxynaphthalene-B-carboxylic acid, and also other orthohydroxy-carboxy compounds capable of coupling, as for example 2-hydroxy-6-methoxynaphthalene-3-carboxylic acid, 2-hydroxyanthracene-3- carboxylic acid, Z-hydroxytriphenylene 3 carboxylic acid, 3-hydroxydiphenylene-oxide-2-carboxylic acid, Z-hydroxycarbazole 3 carboxylic BOzNa SOaNa with an addition of 50 per cent of sodium sulphate (percentages being with reference to the weight of fibres). After powerful rinsing with cold water, the bottomed fabric is treated for half an hour at room temperature'in a neutral solution of the diazo compound of 4-amino-3- methoxydiphenylamine or 4-amino=-4'-methoxydiphenylamine. The dyed fabric is then treated for half an hour at C. in an aqueous bath containing from 1 to 5 grams of soap per litre. ,A navy-blue dyeing of excellent fastness to Washing and very good fastness to light which coversuniformly both kinds of fibre is thus obtained. Dyeings on wool or silk or on mixtures of both may also be prepared in the same way. By using 4-benzoy1amino -2.5-diethoxy- 1 -aminobenzene instead of the said diazo component, a fast blue dyestufi is also obtained; by using 4-chlor-2- aminodiphenyl ether a red dyestufi' is obtained.

Instead of the above described arylide there may be used as coupling component the arylide of the formula:

2. A process of producing fast dyeings on textile material which consists in applying to said 5 material an orthohydroxyl-aryl carboxylicarylide containing in the arylide portion at least one sulfonic acid group and corresponding to the general formula wherein the Ar stands for arylene radicles, and B1, B2 and B3 stand for phenylene radicles, and converting said arylide into a disazo dyestuif by treatment with diazotized aromatic amines.

YAr

3. Disazo dyestuffs corresponding to the general formula N=N-X XN=N OH HO Ar Ar wherein the Ar stands for arylene radicles, and wherein B1, B2 and B3 stand for phenylene radicles and wherein X stands for an aryl radiole.

4. Disazo dyestufis corresponding to the general formula wherein X stands for an aryl radicle.

5. The disazo dyestufl corresponding to the formula N=N--X l HO SOJH SOaH wherein X stands for the radicle of a methoxydiphenylamine.

WOLFGANG ALT. HANS KRZIKALL'A. 

